Design is a meaning and making process that directs emotion, influencesideology, and shapes attitude. We are the subjects of the objectswe make, and when we become the focus of the designed object,the subjective and objective considerations of a design are internallyconnected. As people in a networked society, the borderline betweenusers and objects are being woven together. The aim of this paper is tounderstand the structure of the conflict and the connection between thedifferent aspects of elements in play. The different explorations weavetogether my design work and my artwork in order to develop subjectiveand objective methods for analyzing my ideas. Further to discussand critically evaluate the performance of these two methodologies indetermining whether a subjective question is capable of producing adefined and solvable problem statement. As the culmination of my MFAstudy, the creative work highlights the variations of the design ideologiesI have encountered, and my responses focusing on aspects of identity,empathy, and awareness.